Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles by a Sequential Aza-Wittig/Michael/Isomerization Reaction
Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles by a Sequential Aza-Wittig/Michael/Isomerization Reaction
复制标题
通过顺序 Aza-Wittig/Michael/异构化反应合成 1,2,4,5-四取代咪唑
DOI：
10.1021/jo201846w
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发表时间：
2012-01-06
影响因子：
3.6
通讯作者：
Ding, Ming-Wu
中科院分区：
文献类型：
--
作者：
Nie, Yi-Bo;Wang, Long;Ding, Ming-Wu
由亚磷磷烷3与芳基异氰酸酯的aza-Wittig反应得到的碳二酰亚胺4，在催化量的醇氧钠的存在下与仲胺反应，产率很高，得到1,2,4,5-四取代咪唑7。然而，得到了4-酰基咪唑11，因为苯酚是在催化量的碳酸钾存在下使用的，因为预期的产物10会进一步被空气氧化。
Carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aryl isocyanates, reacted with secondary amines in the presence of a catalytic amount of sodium alkoxide to give 1,2,4,5-tetrasubstituted imidazoles 7 in good yields. However, 4-acylimidazoles 11 were obtained, as phenols were used in the presence of a catalytic amount of potassium carbonate due to further air oxidation of the expected products 10.